NO176440C - Synthetic nonapeptide and decapeptide analogues of LHRH for use in the regulation of fertility and reproductive cycle in humans and livestock - Google Patents

Synthetic nonapeptide and decapeptide analogues of LHRH for use in the regulation of fertility and reproductive cycle in humans and livestock

Info

Publication number
NO176440C
NO176440C NO880494A NO880494A NO176440C NO 176440 C NO176440 C NO 176440C NO 880494 A NO880494 A NO 880494A NO 880494 A NO880494 A NO 880494A NO 176440 C NO176440 C NO 176440C
Authority
NO
Norway
Prior art keywords
phe
ala
naphthyl
alkyl
trp
Prior art date
Application number
NO880494A
Other languages
Norwegian (no)
Other versions
NO176440B (en
NO880494D0 (en
NO880494L (en
Inventor
Jr John J Nestor
Brian H Vickery
Original Assignee
Syntex Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syntex Inc filed Critical Syntex Inc
Publication of NO880494D0 publication Critical patent/NO880494D0/en
Publication of NO880494L publication Critical patent/NO880494L/en
Priority to NO922632A priority Critical patent/NO301014B1/en
Publication of NO176440B publication Critical patent/NO176440B/en
Publication of NO176440C publication Critical patent/NO176440C/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S930/00—Peptide or protein sequence
    • Y10S930/01—Peptide or protein sequence
    • Y10S930/13—Luteinizing hormone-releasing hormone; related peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Endocrinology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Fodder In General (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

Peptides of formula (I) and pharmaceutically acceptable salts are new: A-B-C-Ser-D-E-F-G-Pro-J (I) where A= aminoacyl from D- or L- isomers of: N-Ac-D,L- delta (3,4)-Pro, N-Ac-D,L-Pro, N-Ac-D,L-Phe, N-Ac-D,L- Pcl-Phe, N-Ac-D,L-PF-Phe, N-Ac-3-(1-naphthyl)-D,L-Ala, N-Ac-3-(2-naphthyl)-D,L-Ala and N-Ac-3-(2,4,6-trimethylphenyl)-D,L-Ala; B = D-Phe, D-Pcl-Phe, D-PF-Phe, D-PNO2-Phe, 2,2-diphenylglycyl, D-alpha-methyl-P-cl-Phe or 3-(2-naphthyl)-D-Ala; C= D-Trp, D-Phe, 3-(3-pyridyl)-D-Ala or 3-(2-naphthyl)-D-Ala; D= L-Phe, L-Tyr, 3-(3-pyridyl)-Ala, Arg or G; E= 3-(2-naphthyl)-D-Ala, 3-(3-pyridyl)-D-Ala, D-Tyr, D-Trp, D-nicotinyl-Lys, pyridylacetyl-Lys, D-Glu(AA) or G; F= L-Leu, L-Nle, L-Phe, L-Trp or 3-(2-naphthyl)-L-Ala; G = gp. of formula (IIa), (IIb) or (IIc); n = 1-5; R1 = 1-6C alkyl or fluoroalkyl; R2 = H or R1; or R1-NH-C=NR2 = ring of formula (IIIa), (IIIb) or (IIIc): m = 1-4; A = H or 1-6C alkyl; X = A or halogen; R3 = H, 1-6C alkyl, phenyl or phenyl-lower alkyl; J = D-Ala-NH2, D-Leu-NH2, Gly-NH2 or -NHR4; R4 = lower alkyl or -NHCONH2; D-On(AA) = anisole adduct to D-Glu to form a P-methoxy-phenylketone (at the carboxyl termius of the glutamic acid side chain), i.e. Glu (pMeO-Ph).
NO880494A 1987-02-05 1988-02-04 Synthetic nonapeptide and decapeptide analogues of LHRH for use in the regulation of fertility and reproductive cycle in humans and livestock NO176440C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NO922632A NO301014B1 (en) 1987-02-05 1992-07-03 Analogous Process for Preparing Therapeutically Effective Nonapeptide and Decapeptide Analogs of LHRH

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/010,923 US4801577A (en) 1987-02-05 1987-02-05 Nonapeptide and decapeptide analogs of LHRH useful as LHRH antagonists

Publications (4)

Publication Number Publication Date
NO880494D0 NO880494D0 (en) 1988-02-04
NO880494L NO880494L (en) 1988-08-08
NO176440B NO176440B (en) 1994-12-27
NO176440C true NO176440C (en) 1995-04-05

Family

ID=21748050

Family Applications (3)

Application Number Title Priority Date Filing Date
NO880494A NO176440C (en) 1987-02-05 1988-02-04 Synthetic nonapeptide and decapeptide analogues of LHRH for use in the regulation of fertility and reproductive cycle in humans and livestock
NO922632A NO301014B1 (en) 1987-02-05 1992-07-03 Analogous Process for Preparing Therapeutically Effective Nonapeptide and Decapeptide Analogs of LHRH
NO2001001C NO2001001I1 (en) 1987-02-05 2001-01-16 Ganirelix and its pharmaceutically acceptable salts

Family Applications After (2)

Application Number Title Priority Date Filing Date
NO922632A NO301014B1 (en) 1987-02-05 1992-07-03 Analogous Process for Preparing Therapeutically Effective Nonapeptide and Decapeptide Analogs of LHRH
NO2001001C NO2001001I1 (en) 1987-02-05 2001-01-16 Ganirelix and its pharmaceutically acceptable salts

Country Status (22)

Country Link
US (2) US4801577A (en)
EP (1) EP0277829B1 (en)
JP (1) JPH0791314B2 (en)
KR (1) KR930008095B1 (en)
AT (1) ATE109159T1 (en)
AU (1) AU614275B2 (en)
BR (1) BR1100688A (en)
CA (1) CA1339043C (en)
DE (2) DE3850789T2 (en)
DK (1) DK173544B1 (en)
ES (1) ES2056908T3 (en)
FI (2) FI92326C (en)
HK (1) HK35997A (en)
HU (3) HU215855B (en)
IE (1) IE63707B1 (en)
IL (1) IL85316A (en)
LU (1) LU90657I2 (en)
MX (1) MX9202737A (en)
NL (1) NL300016I2 (en)
NO (3) NO176440C (en)
NZ (1) NZ223403A (en)
ZA (1) ZA88795B (en)

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US4935491A (en) * 1987-08-24 1990-06-19 Board Of Regents, The University Of Texas System Effective antagonists of the luteinizing hormone releasing hormone which release negligible histamine
HU203204B (en) * 1987-09-15 1991-06-28 Sandoz Ag Process for producing suppository containing calcitonin and taurocholic acid
ZA887658B (en) * 1987-10-15 1990-06-27 Syntex Inc Intranasal administration of polypeptides in powdered form
US5110904A (en) * 1989-08-07 1992-05-05 Abbott Laboratories Lhrh analogs
US5039660A (en) * 1988-03-02 1991-08-13 Endocon, Inc. Partially fused peptide pellet
US5137669A (en) * 1988-03-02 1992-08-11 Endocon, Inc. Manufacture of partially fused peptide pellet
WO1990010437A1 (en) * 1989-03-09 1990-09-20 Endocon, Inc. Partially fused peptide pellet
US6156731A (en) * 1989-05-10 2000-12-05 G. D. Searle & Co. Polypeptide composition for oral administration
US5232707A (en) * 1989-07-10 1993-08-03 Syntex (U.S.A.) Inc. Solvent extraction process
US5169932A (en) * 1989-10-30 1992-12-08 The Salk Institute For Biological Studies Gnrh analogs
US5084443A (en) * 1989-12-04 1992-01-28 Biomeasure, Inc. Promoting expression of acetylcholine receptors with lhrh antagonist
US5064939A (en) * 1990-02-06 1991-11-12 The Salk Institute For Biological Studies Cyclic gnrh antagonists
US5212288A (en) * 1990-02-20 1993-05-18 Syntex (U.S.A.) Inc. Temporary minimal protection synthesis of serine-containing polypeptides
DE59100945D1 (en) * 1990-08-04 1994-03-10 Hoechst Ag Gonadoliberin antagonists.
US5783562A (en) * 1990-11-10 1998-07-21 Asta Medica Aktiengesellschaft Luteinizing hormone releasing hormone analogs
CN1036343C (en) * 1990-11-10 1997-11-05 天津市计划生育研究所 Synthesis, products and its application for luleinizing hormone releasing hormone and antagonistic znalogue
IL101074A (en) * 1991-03-14 1997-09-30 Salk Inst For Biological Studi GnRH ANALOGS AND THEIR PREPARATION
DK0593491T3 (en) * 1991-04-25 1997-03-17 Romano Deghenghi Luteinization hormone releasing hormone antagonist peptides
DE4117507A1 (en) * 1991-05-24 1992-11-26 Schering Ag METHOD FOR PRODUCING N (ARROW HIGH) 6 (ARROW HIGH) SUBSTITUTED LYSINE DERIVATIVES
WO1993003752A1 (en) * 1991-08-19 1993-03-04 The Arizona Board Of Regents On Behalf Of The University Of Arizona Decapeptide having dopamine stimulating activity
US5487898A (en) * 1991-08-26 1996-01-30 Abbott Laboratories Compositions and method for the sublingual or buccal administration therapeutic agents
WO1993003751A1 (en) * 1991-08-26 1993-03-04 Abbott Laboratories Compositions and methods for the sublingual or buccal administration of therapeutic agents
US5656727A (en) * 1992-09-15 1997-08-12 The Administrators Of The Tulane Educational Fund Antagonists of LHRH
US5480969A (en) * 1992-09-15 1996-01-02 The Administrators Of The Tulane Educational Fund Antagonists of LHRH
US6828415B2 (en) 1993-02-19 2004-12-07 Zentaris Gmbh Oligopeptide lyophilisate, their preparation and use
DE4305225A1 (en) * 1993-02-19 1994-08-25 Asta Medica Ag New manufacturing process for Cetrorelix lyophilisate
US5843901A (en) * 1995-06-07 1998-12-01 Advanced Research & Technology Institute LHRH antagonist peptides
US6566330B1 (en) * 1996-10-22 2003-05-20 Medical University Of South Carolina Foundation Research Development Positively charged non-natural amino acids, methods of making and using thereof in peptides
US6043218A (en) 1996-10-22 2000-03-28 Medical University Of South Carolina Positively charged non-natural amino acids, methods of making thereof, and use thereof in peptides
US5968895A (en) * 1996-12-11 1999-10-19 Praecis Pharmaceuticals, Inc. Pharmaceutical formulations for sustained drug delivery
DE19712718C2 (en) * 1997-03-26 1999-09-23 Asta Medica Ag Immobilized and activity-stabilized complexes of LHRH antagonists and process for their preparation
DE69831241T2 (en) * 1997-06-20 2006-03-23 Akzo Nobel N.V. Gonadotropin releasing hormone antagonist
US6217844B1 (en) * 1998-04-27 2001-04-17 Praecis Pharmaceuticals, Inc. Methods for detecting lesions in dense breast tissue using LHRH antagonists
US6455499B1 (en) 1999-02-23 2002-09-24 Indiana University Foundation Methods for treating disorders associated with LHRH activity
US6598784B2 (en) * 2000-12-20 2003-07-29 Meadwestvaco Packaging Syatens, Llc Beverage carton with strap type carrying handle
WO2002056903A2 (en) * 2001-01-17 2002-07-25 Praecis Pharmaceuticals Inc. Methods for treating hormone associated conditions using a combination of lhrh antagonists and specific estrogen receptor modulators
GB0320806D0 (en) 2003-09-05 2003-10-08 Astrazeneca Ab Therapeutic treatment
US20060003008A1 (en) 2003-12-30 2006-01-05 Gibson John W Polymeric devices for controlled release of active agents
JP5361210B2 (en) * 2008-02-22 2013-12-04 キヤノン株式会社 Resin composition and molded body
CN102584945A (en) * 2012-02-09 2012-07-18 深圳翰宇药业股份有限公司 Preparation method for ganirelix acetate
CN104231055A (en) * 2013-06-18 2014-12-24 深圳翰宇药业股份有限公司 Ganirelix precursor and method for preparing ganirelix acetate by using ganirelix precursor
CN109443592A (en) * 2018-09-19 2019-03-08 东华大学 A kind of measuring method of temperature sensitive block copolymer lower critical solution temperature
US20220267347A1 (en) 2019-07-29 2022-08-25 Sunshine Lake Pharma Co., Ltd. Substituted pyrimidinedione compounds and uses thereof
WO2023072284A1 (en) 2021-11-01 2023-05-04 山东绿叶制药有限公司 Gonadotropin-releasing hormone antagonist, and preparation method therefor and use thereof

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US4215038A (en) * 1978-10-16 1980-07-29 The Salk Institute For Biological Studies Peptides which inhibit gonadal function
US4419347A (en) * 1980-10-06 1983-12-06 Syntex (U.S.A.) Inc. Nonapeptide and decapeptide analogs of LHRH, useful as LHRH antagonists
US4341767A (en) * 1980-10-06 1982-07-27 Syntex Inc. Nonapeptide and decapeptide analogs of LHRH, useful as LHRH antagonists
US4481190A (en) * 1982-12-21 1984-11-06 Syntex (U.S.A.) Inc. Nonapeptide and decapeptide analogs of LHRH useful as LHRH antagonists
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Also Published As

Publication number Publication date
DE10075027I2 (en) 2004-07-01
NZ223403A (en) 1990-10-26
KR930008095B1 (en) 1993-08-25
IE880298L (en) 1988-08-05
NL300016I1 (en) 2000-11-01
FI92211B (en) 1994-06-30
LU90657I2 (en) 2001-01-15
DK57288A (en) 1988-08-06
FI880509A0 (en) 1988-02-04
HU210819A9 (en) 1995-08-28
EP0277829A2 (en) 1988-08-10
EP0277829B1 (en) 1994-07-27
AU614275B2 (en) 1991-08-29
FI930694A0 (en) 1993-02-17
IE63707B1 (en) 1995-05-31
ZA88795B (en) 1989-10-25
IL85316A0 (en) 1988-07-31
IL85316A (en) 1992-07-15
DK57288D0 (en) 1988-02-04
NO2001001I1 (en) 2001-02-05
JPS63201199A (en) 1988-08-19
FI92326B (en) 1994-07-15
NO922632D0 (en) 1992-07-03
FI92326C (en) 1994-10-25
HU215855B (en) 2001-02-28
US5767082A (en) 1998-06-16
HUT46340A (en) 1988-10-28
KR890013060A (en) 1989-09-21
US4801577A (en) 1989-01-31
DE10075027I1 (en) 2000-11-30
HUT63855A (en) 1993-10-28
DK173544B1 (en) 2001-02-19
FI930694A (en) 1993-02-17
MX9202737A (en) 1992-06-30
BR1100688A (en) 2000-04-18
DE3850789D1 (en) 1994-09-01
NO176440B (en) 1994-12-27
DE3850789T2 (en) 1995-03-09
NO301014B1 (en) 1997-09-01
NL300016I2 (en) 2001-01-02
FI880509A (en) 1988-08-06
CA1339043C (en) 1997-04-01
FI92211C (en) 1994-10-10
AU1126588A (en) 1988-08-11
ATE109159T1 (en) 1994-08-15
EP0277829A3 (en) 1990-10-31
NO880494D0 (en) 1988-02-04
NO922632L (en) 1988-08-08
JPH0791314B2 (en) 1995-10-04
NO880494L (en) 1988-08-08
HK35997A (en) 1997-03-27
ES2056908T3 (en) 1994-10-16

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